175844-54-9

Basic information

• Product Name: 6-bromo-2,3-dimethoxybenzyl bromide
• Synonyms: 6-bromo-2,3-dimethoxybenzyl bromide
• CAS NO: 175844-54-9
• Molecular Weight: 309.985
• Mol File: 175844-54-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6-bromo-2,3-dimethoxybenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2,3-dimethoxybenzyl bromide(175844-54-9)
• EPA Substance Registry System: 6-bromo-2,3-dimethoxybenzyl bromide(175844-54-9)

Safety Data

• Hazardous Substances Data: 175844-54-9(Hazardous Substances Data)

Upstream product

• 74866-17-4 3,4-dimethoxy-2-methyl-1-bromobenzene 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 107290-27-7 (6-bromo-2,3-dimethoxyphenyl)methanol 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 34316-15-9 chelerythrinium 
• 15575-49-2 6-acetonyldihydrochelerythrine 
• 1449388-39-9 N-(6-bromo-2,3-dimethoxybenzyl)-N-(naphtho[2,3-d][1,3]dioxol-5-yl)benzamide 
• 1407973-55-0 C₁₃H₁₇BrO₅ 
• 1407973-54-9 C₁₃H₁₇BrO₅ 
• 1407973-56-1 C₁₂H₁₅BrO₅ 
• 1407973-57-2 C₁₂H₁₅BrO₅ 
• 1018331-27-5 C₁₃H₁₆BrNO₄ 
• 1018331-30-0 C₁₂H₁₄BrNO₃S 
• 1018331-23-1 C₁₂H₁₄BrNO₄ 
• 238754-87-5 (E)-6-hydroxymethyl-2,3,3',4'-tetramethoxystilbene 
• 238754-85-3 (E)-6-formyl-2,3,3',4'-tetramethoxystilbene 
• 238754-84-2 (E)-6-bromo-2,3,3',4'-tetramethoxystilbene 
• 96552-45-3 (E)-3-(2-((E)-3,4-dimethoxystyryl)-3,4-dimethoxyphenyl)acrylic acid 

Relevant articles and documents

Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents

A convenient route was envisaged toward the synthesis of dihydrochelerythrine (DHCHL), 4 by intramolecular Suzuki coupling of 2-bromo-N-(2-bromobenzyl)-naphthalen-1-amine derivative 5 via in situ generated arylborane. This compound was converted to (±)-6-acetonyldihydrochelerythrine (ADC), 3 which was then resolved by chiral prep-HPLC. Efficiency of DHCHL for the stabilization of promoter quadruplex DNA structures and a comparison study with the parent natural alkaloid chelerythrine (CHL), 1 was performed. A thorough investigation was carried out to assess the quadruplex binding affinity by using various biophysical and biochemical studies and the binding mode was explained by using molecular modeling and dynamics studies. Results clearly indicate that DHCHL is a strong G-quadruplex stabilizer with affinity similar to that of the parent alkaloid CHL. Compounds ADC and DHCHL were also screened against different human cancer cell lines. Among the cancer cells, (±)-ADC and its enantiomers showed varied (15-48%) inhibition against human colorectal cell line HCT116 and breast cancer cell line MDA-MB-231 albeit low enantio-specificity in the inhibitory effect; whereas DHCHL showed 30% inhibition against A431 cell line only, suggesting the compounds are indeed cancer tissue specific.

The total synthesis of salvianolic acid F

An expeditious synthesis of salvianolic acid F 2 is described in 10% overall yield. Tetramethyl salvianolic acid F 3 was obtained in six steps in 39% overall yield and was converted into the target molecule using boron tribromide in 26% yield.